


It's Better When Anticipated

by auntieshakespeare



Category: Supernatural
Genre: Alternate Universe, M/M, Porn With Plot, Porn with Feelings
Language: English
Status: Completed
Published: 2018-05-07
Updated: 2018-05-07
Packaged: 2019-05-03 09:43:24
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,179
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14566305
Author URL: https://archiveofourown.org/users/auntieshakespeare/pseuds/auntieshakespeare
Summary: Dean wants Benny and Cas to move in. Sam just wants to get fucked. Porn ensues. Amazingly, so do feelings.(In which Sam confronts his brother and their roommates about their constant violation of his boundaries and after much sharing and caring, he gets dicked three ways to Sunday.)





	It's Better When Anticipated

**Author's Note:**

> When I started this back in March it was supposed to be a short PWP featuring Sam getting triple dicked. Somehow it turned into 4k+ words of mostly sexual tension and insecurity. Welp. It'll do.
> 
> Unbeta'd and written on my ever frustrating tablet, so if there are any glaring errors, I'm sorry. I've got clumsy fingers and a bad relationship with technology.
> 
> (Oh yeah, um this is set in kind of an AU. The Winchesters are still hunters, but Mary and John are alive and the supernatural is well known to all. Not super relevant to the story, but jsyk.)
> 
> Title taken from Morningwood's "Take Off Your Clothes."

Sam is an open minded guy. Truly.

When you grow up in a family with two psychic honorary aunts and ghosthunting parents, it's hard to get too caught up in dogma. Factor in psychic abilities of his own, a time travelling grandfather, and you know, fraternal incest and Sam is fairly certain he has this whole unorthodox lifestyle thing pretty much set. But Dean. Of course, Dean. Dean has to shake everything up again with his innocent suggestions and stupidly fuckable mouth.

"Cas and Benny should move in, don't ya think?" he'd asked as the men entered their shared apartment one night, before dropping to his knees and grinning up at Sam, right hand unbuttoning Sam's jeans while his left just. Stroked. 

(Sam is not the kind of man who can be led around by his dick. Mostly.)

"Don't we see enough of your friends without them living with us?" Sam had asked, valiantly trying to ignore the throbbing of his rapidly hardening cock in Dean's hand. He had more to say, didn't spend the better part of a decade perfecting his rebuttals at 31k a semester for nothing, but Dean chose that moment to wrap his lips around Sam's dick and he yielded the floor to the opposition. 

Dean knew all of his arguments anyway. Lead on, dick.

Five minutes later and Sam had shot all of his arguments and the last of his willpower down his brother's throat. He collapsed into a brainless, boneless pile against a living room wall. Dean, the conniving bastard, took advantage of his momentary incapacitation to drive the point home.

"First off, Cas is _our_ friend and he's trying to spend more time on Earth now that Heaven has worked out their issues in upper management. He doesn't have anywhere to stay and it's not like being a seraph really pays." At this, Dean snorted, stretching his long body out like a cat across their living room floor before briefly casting his eyes skyward. "Plus Benny's been havin' a rough go at it since his great-grand NILF moved back to Lousiana. And he's on bagged blood, so it's not like we gotta worry about him sniffing around our necks when he gets thirsty. C'mon, Sammy don't be selfish. You love strays. Think of them as two big, socially backwards puppies." 

Sam, knowing when Dean had already made up his mind, accepted this spiel as the courtesy warning it was and sighed, slumped against the wall, soft dick still hanging out of his pants. "Okay, but you're cleaning up any accidents they have in the house."

At that Dean had grinned and tucked Sam back into his jeans, pressing a soft kiss into his neck as he did. "I'll make sure to buy the extra large puppy pads, princess."

That was a month ago and Sam has started to think he needs to revisit this whole open minded thing because, his roommates are definitely trying to kill him via sexual frustration. 

When it came to Dean, well that was just par for the course. His brother has always been charming and personable, using every one of his natural born gifts to entice and distract. Be it convincing a police officer that an obviously stolen car was his legal property or smooth talking a cougar into buying him drinks all night, he can flirt and fabricate his way in and out of any situation. (See: blowjobs for roommates.) But ever since Cas and Benny moved in it's like it's become a goddamn superpower. Every time Sam thinks to seek Dean out to complain he is coincidentally naked, wet, naked AND wet, or artfully covered in some kind of grime that only looks good on him. 

However, despite all the sex appeal, there was little sex to be had. Dean had taken several long hunts in various neighboring states and when he was home all he ever seemed to do was hang around with their new roommates. Mostly shirtless. Sometimes pantless. 

And maybe, _maybe_ if it was just Dean, Sam would be okay. Yeah he'd be jacking off in the shower more than usual, but he'd still have a sense of equilibrium. But Cas and Benny? They're even worse.

***

On a good day Castiel has no sense of personal space. But since moving semi-permanently to Earth, it seems like his mission has been changed from "Watch humanity" to "Always be within touching distance of Sam Winchester's ass." 

It started off innocuous enough, little things like bumping into each other in the kitchen, brushing past each other in the hall. Things Sam would write off entirely were it not for the way goosebumps would ripple across his skin and the way Cas' hand always _miraculously_ ended up cupping his ass as they passed. 

Case in point: he'd been brushing his teeth after a draining day at the office, eyes closed in an attempt to fend off the kind of headache that only came with a skinwalker case when suddenly a tingle ran up his neck and a warm, heavy weight pressed up behind him. 

Spitting into the sink, Sam sighed, "Cas, dude, we've talked about this, personal sp-" 

Smooth fingers traced up his back under his shirt, cutting his protest short. 

"You carry so much tension in your back," Cas murmured, running his fingers down Sam's spine before both hands gripped his hips, pressing him into the porcelain sink and holding him there, firm but without threat. Sam could easily work himself out of his position if he wished, but found himself breathless, captured by the moment. He stared into the mirror, into Cas' reflection molded against his back and shivered. The angel's expression never faltered, but the inhuman blue of his eyes darkened as his pupils dilated, predatory and oh so pleased.

"Your brother says it's because work yourself too hard and I'm inclined to agree," Cas said, voice lowering to a gravelly bass as his hands shifted from Sam's hips to his ass, "He also says it's because you occasionally have a rather large stick lodged in your rectum. I'm not certain I believe the latter claim, but I'm willing to investigate it anyway. If it's true, we should really do something about that." And with that he was gone, the flutter of angel wings and a low ache in Sam's groin the only indications that anyone had been with him at all.

***

If Dean was temptation and Cas a tease, then Benny was trouble. The man was always watching, eyes bright and covetous. He leaned in the doorway while Sam did the dishes, a hungry presence at Sam's back. No space was too sacred to invade, not even the shower and hadn't _that_ been a surprise.

Sam had found himself with a rare afternoon off and a seemingly empty apartment (and oh how he missed solitude, so impossible to find nowadays) and was determined to enjoy every second of it. After spending a few hours laying around flitting from this to that he felt inspired to hop into the shower and simply exist for an hour. Finished soaping up his torso, Sam found his fingers circling his hole and gave in to the desire that had been building up over his long, Deanless weeks. Sex had been more or less absent from his life since The Roomate Blowjob Bribe and while he didn't _need_ sex the way Dean seemed to, he did miss it.

One finger became two became three and Sam was lost in the sensations. The sharp pleasure when he hit his prostate was eclipsed by how good it felt to be full again, fingers thrusting in and out but never fully withdrawing. He pressed his forehead against the slick wall of the shower, closing his eyes as he worked himself closer and closer to--

"Pardon me, cher," a rumbling voice drawled unexpectedly close to Sam's ear, "I'd have waited a little longer if I'd known you were puttin' on a show in here."

Sam whipped his head to the side, withdrawing his fingers so hard it hurt. Benny was grinning at him, parted shower curtain in his grip--and when had _that_ happened?--eyes shiny with mirth and something undefinable. 

"What the hell?" Sam spluttered, getting a mouthful of water for his troubles. 

"Didn't mean to bother you, but-"

"But you did, jesus" Sam shouted, fury rising in his chest. "Look I get that the universe and everyone in it seems to think that my personal boundaries are less important than theirs, but I'd like to do something for myself once in a while without being scrutinized!"

He's not sure what he expected, embarrassment and frustration clouding his brain, but it wasn't this. Benny didn't sneer, didn't rage, didn't recoil. Instead he nodded, expression unreadable, and walked away. As his anger cooled, Sam found himself being pounded in the head with lukewarm water still sporting an erection that hadn't flagged and a growing sense of confusion. 

Shutting off the water, Sam came to a decision. Something had to give. Benny and Cas had to go. 

***

Thus Sam stood in front of the door to his apartment contemplating. It had been more or less all he had been doing all day. Thinking. Planning. Worrying. How was he going to get Dean alone in an apartment full of creatures with superior senses and no sense of privacy? How would Dean take his concerns? What if he shut Sam out? And what about his own doubts? 

Sure, there were the numerous bathroom violations, but it wasn't all groping and voyeurism. There were movie nights pressed between Dean and Cas, Benny by his legs on the floor rubbing his sore feet. Cas was teaching him Enochian and Sam was teaching him Klingon in return. There were days where he'd watch Dean and Cas from across the apartment, jealousy bubbling in his guts and Benny would sit down beside him with a pack of playing cards and a fifth of whiskey and in a matter of minutes their home would be full of laughter and warmth. 

_You're selfish_ he thought, clearing his throat before turning the doorknob, _selfish and weak._

Any hopes for a private conversation flew out the window when he opened the door to reveal all three of his roommates sitting on the couch like they were waiting for him. Dean sat in the middle, elbows resting on his spread legs, face impassive. Cas sat to his left, turned slightly to face Dean, eyes set soft and concerned. Benny was perched on the arm of the couch to Dean's right, leaving an empty cushion between them, a small upturn to his lips. Three sets of eyes were trained on Sam as he shut the door behind him.

"Is this an intervention? 'Cause I kicked the demon blood habit back in law school, so you're a few years late on that." Joking around to mask anxiety was a trick he learned from Dean, and from the look on his face, he was none too impressed with the act.

"Sammy-"

He cut Dean off, heart beating erratically. This suddenly seemed like a very bad idea. "Dean, look, I'm sorry I've been such a-"

In the span of one uneven heartbeat Dean crossed the room, taking Sam's face into his hands. "Sam, please. Listen to me. We want to apologize." 

"What, what are you talking about? I'm the one who's been a jerk." 

From the couch Castiel let out a heavy sigh. "No Sam, it's we who've wronged you. Please, let your brother explain."

Face still cupped in his brother's hands, Sam wet his lips and closed his eyes, releasing the breath that had been caught in his chest since he touched the door. "Okay, alright. I'm. I'm ready to hear this." He wasn't. He didn't know what Cas meant when he said they had wronged him, but from the angel's hang-dog expression and the nerves he felt Dean practically vibrating with, he could guess. Sam didn't have to worry about asking the other's to leave. They were kicking him out.

The sensation of lips pressing against his forehead startled him out of his despair. Dean repeated the kiss against his hands, releasing his face and leading him towards the empty cushion next to Benny. He sat down with a quick glance up at the vampire, whose expression was now schooled into one of complete blankness.

"Look, I suck at apologies, so this is probably gonna be complete shit but. Sam, I know you've been...unhappy with this set up and. God, I'm sorry. We thought it would be easier this way, you know? If we started off by having everyone around first before..." Dean trailed off, looking to Castiel for help. Sam didn't need to hear it. He was pretty sure he had figured it out for himself.

Yanking his hand out of Dean's grip, he hissed, "So this is it? Invite Cas and Benny to live with us so I can acclimate to, what? Them taking my place in your life? And the sexual harrassment has been what, taunting?"

"Sam, no-"  
"What, Sammy-"

Dean and Castiel's protestations stumbled over each other, but it was Benny who commanded Sam's attention. Pulling his hand from his lap, he threaded his fingers through Sam's hair before purring, "Oh no, cher, do you have this situation all twisted about. They ain't apologizin' for tryin' ta leave you. They're apologizin' for the piss poor way we've been tryin' ta get you into bed with us."

There was a brief, very stunned silence that was broken by Dean groaning.

"I wasn't gonna be that blunt about it, but. Yeah." He ran a hand through his hair, grinning over at Benny, "Less Intervention, more, I dunno, Sister Wives. Minus any religious implications. Mostly." At this he nodded to Castiel, who at least had the decency to look a little sheepish.

A breathy noise escaped Sam's mouth, somewhere between a sigh and a grunt. "I'm...not sure I understand. All of this is because you...wanna have a foursome?"

Dean opened his mouth, but Cas put a silencing hand on his lap. "Benny and I understand that you and Dean have a very deep, very intimate bond and we would never want to interfere with that. However, over the years of working with the two of you we've developed...feelings."

"Desires," Benny added. "Fantasies, if you'd like. I sure would." He winked at Sam and things were no less confusing or urgent, but the feelings behind the urgency were changing shape. The room was warm, so warm suddenly.

"Cas came to me after a hunt about a year ago. He was upset." Dean smiled softly at the memory. "He was ashamed. Said that he was feeling confused about us and our place in his life." He took Cas' hand and pressed a kiss to it, gentle and fond like he had to Sam's. "Thought it was sin, the way he felt. Thought he was falling."

At this Cas slid from the couch, onto the floor at Sam's feet. "I thought I was falling from grace. Dean told me that I was falling in love. With you. With both of you." Reaching up, he cupped Sam's face with his left hand and pressed Sam's hand against his heart with his right. "It was wrong of me to engage with you physically before you knew what you meant to me here. You and Dean have been my heart since I was given my assignment on Earth."

And what could he say to that? An angel on his knees before him, confessing his love. A love reciprocated. Dean and Sam had been lovers long before they knew the taboo of it, but Castiel had found them when they were barely men themselves. The bond of those years, hunts and addictions, graduations, weddings, funerals, late nights and early mornings. Castiel was as surely a part of Sam's soul as Dean was. But Sam carried guilt like an anchor, heavy and steadfast around his neck and never spoke a word of it to anyone. Still it seemed they knew just the same.

It was all too much to process in the moment, so Sam turned to Benny, shrugging free of his hand and asked, "And I suppose you're in love with my brother and I too?"

Benny grinned, teeth sharp and bright. "Nah, cher. This ol' dusty heart isn't good for much anymore. But I'm more than enamored with the way your neck looks all flushed and bared."

"And all the grab ass?"

Dean blushed, an embarrassed laugh escaping him. "You have this kinda prudish facade, yanno? You wanna act all vanilla, but you're a stone cold freak in the bedroom. I thought maybe we pushed you a little you'd ask what's up."

At this, Sam shook his head. "I was confused. And uncomfortable. And that's...that's never really been something you've cared about before."

Dean looked stricken, but wisely chose to let Sam continue.

"I wasn't sure what was going on, but I was frustrated by it and," he looked down to Cas, the only one he trusted not to leer, "kind of turned on?"

Sure enough, he could feel the dual smirks of his brother and Benny on either side of him, but Castiel just smiled. 

"I'm pleased. And sorry. It was deceptive on our part and could have ruined everything we had hoped to build between us. But it wasn't wholly unsuccessful?"

The thermostat had to be broken. The room was sweltering. Surely he wasn't the only one feeling so flushed.

With a sigh he closed his eyes and murmured, "No, I'd say you finally accomplished your goal."

"You hear that, brother? Our Sam says we've finally done something right." The warm, Cajun drawl sent tingles down Sam's spine, a balm to ease the heat that had encased his body.

"You haven't done anything yet."

Three sets of lips turned upward and the suffocating heat returned. Dean's lips dragged against Sam's ear as he whispered.

"Just say the word and we'll do _anything_."

The word _Yes_ came to mind. _Now_ was also a strong contender. But what escaped Sam's lips, desperate and longing was:

"Please."

***

Later none of them would be able to say how they made it from couch to bedroom. Sam had a vague memory of being hefted up by Benny, cool and solid against his chest, but the journey down the hall was lost to mouths. Mouths pressed against his, tongues tangling, teeth catching lips and _tugging_. Mouths against his back, his neck, the graceful slope where the two met. Shirts lost down the hall. Pants lost in the doorway. And hands.

Hands gliding up and down his torso. One pressed against firm abs while another slides down his back to cup his ass. One holding his face still while someone sucks a mark into his neck. Another still jacking him gently while fingers trace the soft, ticklish part of his inner thigh. A voice from behind him whispers low and hungry into his ear.

"We're gonna wreck you, baby boy." Dean, then.

Dean's calloused fingers pull away from Sam's body and he moans his protestations before hearing the quiet _snick_ of a cap open and close. The fingers return, just one at first, rubbing gentle circles around Sam's hole. A finger dips in just as a wet, warm mouth closes on his dick. The choreography is spectacular and Sam is never going to be sane ever again. He's going to go sex-mad and it will be all Dean's fault.

The hand on his jaw releases him, mouth moving down to his nipples, so Sam drops his gaze to find Cas staring up at him from his knees, mouth wrapped around Sam's cock. He reaches into the dark mop of hair and tugs, beckoning the angel up for a kiss. They trade messy, open mouthed kisses for some time while Dean works a steadily growing number of fingers into Sam's ass. Periodically Benny will cut in, catching the mouth of whoever he can, mouthing against Sam's neck when he can't and jacking Dean's dick all the while. 

Finally, dear god finally Dean withdraws his fingers and asks, "You ready, Sammy?"

Dazed, Sam just nods. He loses time again, brief patches. One minute he's caught between his three lovers, the next he's on his hands and knees on the bed, Dean behind him, pumping into his ass like a fucking piston. Benny is in front of him, dick down his throat. Castiel is lain beneath him, legs spread wide--Benny between them--sucking Sam despite the frenetic pace Dean is setting. He remembers Dean finishing, grabbing his long hair and pulling, pressing a lingering kiss to his sweaty neck but then--

Benny is fucking Cas, Cas who is suckling Sam's dick like it's vital fucking nourishment and Sam can't breathe even though his mouth is empty because Dean is. Dean is _sucking his come out of Sam's ass_ and Sam is gasping, clenching, spurting down the throat of an angel who looks so beyond blissed he may as well have fallen from grace. It's too much, it's not nearly goddamn enough and then--

Benny is deep inside him, thicker than Dean, but cooler too and it's strange but not offputting. Cas is rubbing the head of his cock against Sam's lips, tracing endless circles. He dips into Sam's willing mouth, pumps, then withdraws. Sam thinks he may be crying, because Dean is kneeling next to him, pushing his long hair out of his face and wiping his cheeks, pressing kisses into his neck. Whispering. 

_Sammy, thank you. Sam this is perfect. Baby boy, you are beautiful. Sam, I love you so much._

He remembers Benny coming with a growl, very human teeth biting into the meat of his shoulder. He remembers the dark look in Cas' eyes and thinks _I'd Fall for him_. He's hefted up into a kneeling position, legs on the bed, chest exposed. Castiel takes his place behind him, slides into him with ease. Dean meets him chest to chest, eye to eye, mouth to mouth. Their spent dicks rub against one another, sparks pulsing inside as they do. Benny settles in behind Dean, arms wrapping around his waist, nipping up his neck. Insatiable.

Sam tries to take it all in--they make a gorgeous view--but with every pump Castiel whispers into Sam's ear and the world quickly becomes nothing but pressure and sound.

_This body is perfect, Samuel. Of course it is, it's made in my Father's image. But there are billions of perfect bodies in this world and none of them compare to you. Your compassion, your patience, your curiosity, your selflessness. These things are what make you beautiful. The light in your eyes when you make a break in a case. The way your body trembles as you find release. These are the memories I will carry with me into battle. My Father was right when He told us to worship humans as we would Him. You are Divine._

Cas tucks a kiss into the nape of Sam's neck, damp with sweat and marked with a hundred kisses and comes with a wave of energy that knocks the four of them to the bed. Cas topples to the floor, but Sam is too fucked out to move or even speak. Dean chuckles, pressing a quick kiss to Sam's mouth before reaching across his stunned brother to help the angel back onto the bed. 

They settle in, four men in a queen sized bed that is covered in three kinds of bodily fluid. Benny lays on his back, one arm folded behind his head, Dean tucked under the other. Sam is draped across Dean chest to chest, still fuck-stupid and blinking mindlessly. He registers, vaguely, that one arm is pulled up above his head and the other folded up to touch Dean. Castiel is snuggled in on his other side, his warm chest against Sam's side. Despite their exhaustion, they only doze.

When Sam wakes up, finally pulled from the mental peace that only the well fucked inhabit, he takes in his surroundings.

There's a dent in the wall near the door and a mound of pants in the doorway. Dean has one sock still on his foot. The sheets, filthy and a little damp, are attached by only one corner. Benny's lower body is slowly sliding off the bed and Cas seems to be using his grace to stay on the tiniest sliver of bed he's occupying. Sam's feet are dangling off the foot of the bed and every muscle in his body _aches_. Groaning, he rolls off of Dean and onto his back, knocking Cas off the bed, who makes a noise that startles Benny onto the floor.

Sighing, Sam tucks himself into Dean, worn out and satisfied. Turns out he is pretty damn open minded. Before the world fades into dreams, Sam murmurs into his brother's neck.

"We've gotta get a bigger bed."

**Author's Note:**

> It's been five years since I've written fanfiction (thanks, depression!) and I am still kinda shocked I managed to finish this. Also, I'm super duper ace, so I hope the sex was satisfactory. 
> 
> Thanks for reading.


End file.
